钌(II)-吡啶基NNN配合物催化酮的室温(不对称)氢转移反应

doi:10.1016/S1872-2067(12)60583-X

催化学报

钌(II)-吡啶基NNN配合物催化酮的室温(不对称)氢转移反应

杜旺明, 王清福, 余正坤

中国科学院大连化学物理研究所, 辽宁大连 116023

收稿日期:2013-03-07 修回日期:2013-03-21 出版日期:2013-07-16 发布日期:2013-07-16
通讯作者: 余正坤
基金资助:
国家重点基础研究发展计划(973计划, 2009CB825300).

Ru(II) pyridyl-based NNN complex catalysts for (asymmetric) transfer hydrogenation of ketones at room temperature

DU Wangming, WANG Qingfu, YU Zhengkun

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2013-03-07 Revised:2013-03-21 Online:2013-07-16 Published:2013-07-16
Supported by:
This work was supported by the National Basic Research Program of China (973 Program, 2009CB825300).

摘要/Abstract

摘要： 合成了一种基于吡啶骨架含有苯并咪唑和手性咪唑啉基团的三齿NNN配体及其二价钌(II)配合物,通过核磁共振波谱学和X射线单晶晶体结构测定确认了钌(II)配合物的分子结构.这些配合物在室温下催化酮的氢转移反应,表现出了优异的催化活性,收率和ee值最高分别可达99%和97%.

关键词: 钌(II)配合物, 不对称氢转移, 手性咪唑啉, 苯并咪唑, 酮

Abstract: Ru(II) complexes bearing pyridyl-based benzimidazolyl-imidazolinyl tridentate NNN ligands were synthesized and structurally characterized. Their molecular structure was confirmed by X-ray crystallography. These complexes demonstrated good to excellent catalytic activity in the asymmetric transfer hydrogenation of ketones at room temperature, achieving up to 99% yields and 97% ee values.

Key words: Ru(II) complex, Asymmetric transfer hydrogenation, Chiral imidazolinyl, Benzimidazolyl, Ketone

杜旺明, 王清福, 余正坤. 钌(II)-吡啶基NNN配合物催化酮的室温(不对称)氢转移反应[J]. 催化学报, DOI: 10.1016/S1872-2067(12)60583-X.

DU Wangming, WANG Qingfu, YU Zhengkun. Ru(II) pyridyl-based NNN complex catalysts for (asymmetric) transfer hydrogenation of ketones at room temperature[J]. Chinese Journal of Catalysis, DOI: 10.1016/S1872-2067(12)60583-X.

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参考文献

[1] Jacobsen E N, Pfaltz A, Yamamoto H. Comprehensive Asymmetric Catalysis I-III. Berlin: Springer-Verlag, 1999. 199

[2] Moore C M, Szymczak N K. Chem Commun, 2013, 49: 400

[3] Sorribes I, Wienhöer G, Vicent C, Junge K, Llusar R, Beller M. Angew Chem, Int Ed, 2012, 51: 7794

[4] Steward K M, Gentry E C, Johnson J S. J Am Chem Soc, 2012, 134: 7329

[5] Vázquez-Villa H, Reber S, Ariger M A, Carreira E M. Angew Chem, Int Ed, 2011, 50: 8979

[6] Alonso F, Riente P, Yus M. Acc Chem Res, 2011, 44: 379

[7] Malacea R, Poli R, Manoury E. Coord Chem Rev, 2010, 254: 729

[8] Bart髃 M. Chem Rev, 2010, 110: 1663

[9] Ikariya T, Blacker A J. Acc Chem Res, 2007, 40: 1300

[10] Noyori R, Hashiguchi S. Acc Chem Res, 1997, 30: 97

[11] Baratta W, Herdtweck E, Siega K, Toniutti M, Rigo P. Organometallics, 2005, 24: 1660

[12] Baratta W, Ballico M, Chelucci G, Siega K, Rigo P. Angew Chem, Int Ed, 2008, 47: 4362

[13] Baratta W, Chelucci G, Herdtweck E, Magnolia S, Siega K, Rigo P. Angew Chem, Int Ed, 2007, 46: 7651

[14] Baratta W, Chelucci G, Gladiali S, Siega K, Toniutti M, Zanette M, Zangrando E, Rigo P. Angew Chem, Int Ed, 2005, 44: 6124

[15] Mikhailine A A, Maishan M I, Lough A J, Morris R H. J Am Chem Soc, 2012, 134: 12266

[16] Sonnenberg J F, Coombs N, Dube P A, Morris R H. J Am Chem Soc, 2012, 134: 5893

[17] Touge T, Hakamata T, Nara H, Kobayashi T, Sayo N, Saito T, Kayaki Y, Ikariya T. J Am Chem Soc, 2011, 133: 14960

[18] DÍaz-Valenzuela M B, Phillips S D, France M B, Gunn M E, Clarke M L. Chem Eur J, 2009, 15: 1227

[19] Lundgren R J, Rankin M A, McDonald R, Schatte G, Stradiotto M. Angew Chem, Int Ed, 2007, 46: 4732

[20] Hayes A M, Morris D J, Clarkson G J, Wills M. J Am Chem Soc, 2005, 127: 7318

[21] Du W M, Wang L D, Wu P, Yu Z K. Chem Eur J, 2012, 18: 11550

[22] Zhao M, Yu Z K, Yan S G, Li Y. J Organomet Chem, 2009, 694: 3068

[23] Zeng F L, Yu Z K. Organometallics, 2008, 27: 6025

[24] Yu Z K, Zeng F L, Sun X J, Deng H X, Dong J H, Chen J Z, Wang H M, Pei C X. J Organomet Chem, 2007, 692: 2306

[25] Zeng F L, Yu Z K. J Org Chem, 2006, 71: 5274

[26] Deng H X, Yu Z K, Dong J H, Wu S Z. Organometallics, 2005, 24: 4110

[27] Jin W W, Wang L D, Yu Z K. Organometallics, 2012, 31: 5664

[28] Zeng F L, Yu Z K. Organometallics, 2009, 28: 1855

[29] Zhao M, Yu Z K, Yan S G, Li Y. Tetrahedron Lett, 2009, 50: 4624

[30] Zeng F L, Yu Z K. Organometallics, 2008, 27: 2898

[31] Ye W J, Zhao M, Yu Z K. Chem Eur J, 2012, 18: 10843

[32] Ye W J, Zhao M, Du W M, Jiang Q B, Wu K K, Wu P, Yu Z K. Chem Eur J, 2011, 17: 4737

[33] Liu H, Du D M. Adv Synth Catal, 2009, 351: 489

[34] Menges F, Neuburger M, Pfaltz A. Org Lett, 2002, 4: 4713

[35] Mei L Y, Yuan Z L, Shi M. Organometallics, 2011, 30: 6466

[36] Hyodo K, Nakamura S, Shibata N. Angew Chem, Int Ed, 2012, 51:10337

[37] Wu L Y, Hao X Q, Xu Y X, Jia M Q, Wang Y N, Gong J F, Song M P. Organometallics, 2009, 28: 3369

[38] Enthaler S, Hagemann B, Bhor S, Anilkumar G, Tse M K, Bitterlich B, Junge K, Erre G, Beller M. Adv Synth Catal, 2007, 349: 853

[39] Bhor S, Anilkumar G, Tse M K, Klawonn M, Dobler C, Bitterlich B, Grotevendt A, Beller M. Org Lett, 2005, 7: 3393
[40] Ma K Y, You J S. Chem Eur J, 2007, 13: 1863

钌(II)-吡啶基NNN配合物催化酮的室温(不对称)氢转移反应

Ru(II) pyridyl-based NNN complex catalysts for (asymmetric) transfer hydrogenation of ketones at room temperature

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